Water → N-(1-Ethyl-1H-pyrazol-3-yl)-3-[(9-fluoro-4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-5-{[(S)-1-methyl-2-(methyloxy)ethyl]oxy}benzamide

HRID 548704Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 548704
CC([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]([CH3:21])[C:10](=[O:20])[C:11]1[CH:16]=[CH:15][C:14](F)=[C:13]([F:18])[C:12]=1F)(C)C.[CH2:24]([N:26]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:46])[C:33]2[CH:38]=[C:37]([O:39][C@@H:40]([CH3:44])[CH2:41][O:42][CH3:43])[CH:36]=[C:35]([OH:45])[CH:34]=2)=[N:27]1)[CH3:25].C(=O)([O-])[O-].[K+].[K+].O>CC(N(C)C)=O>[CH2:24]([N:26]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:46])[C:33]2[CH:38]=[C:37]([O:39][C@@H:40]([CH3:44])[CH2:41][O:42][CH3:43])[CH:36]=[C:35]([O:45][C:14]3[CH:15]=[CH:16][C:11]4[C:10](=[O:20])[N:9]([CH3:21])[CH2:8][CH2:7][O:6][C:12]=4[C:13]=3[F:18])[CH:34]=2)=[N:27]1)[CH3:25]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 57663171N-(2-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}ethyl)-2,3,4-trifluoro-N-methylbenzamideHCID 59127176N-(1-Ethyl-1H-pyrazol-3-yl)-3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}benzamide

Produkt 1

HCID 15949499N-(1-Ethyl-1H-pyrazol-3-yl)-3-[(9-fluoro-4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-5-{[(S)-1-methyl-2-(methyloxy)ethyl]oxy}benzamideAusbeute 68,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A suspension of N-(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)-2,3,4-trifluoro-N-methylbenzamide (300 mg, 0.86 mmol), N-(1-ethyl-1H-pyrazol-3-yl)-3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}benzamide (290 mg, 0.91 mmol) and potassium carbonate (237 mg, 1.73 mmol) in DMA (20 mL) was heated to 140° C. for 4 hours. The reaction was poured into water (100 mL) and extracted with ethyl acetate (3×50 mL). The combined organic phases were washed with brine (50 mL) and dried (MgSO4), filtered and evaporated to give an orange oil. This was purified by column chromatography on alumina, eluting with 30-100% ethyl acetate in isohexane, to give the desired product as a colourless oil (300 mg).

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organic phases were washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give an orange oil
  7. customThis was purified by column chromatography on alumina
  8. washeluting with 30-100% ethyl acetate in isohexane

Quellen und Nachweise

ORD-Eintrag
ord-41f3497112704fce96f3dcc55df72470
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943607B2

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